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During a rough adolescence, detailed in many of his autobiographical songs, Shawn Carter dealt drugs and flirted with gun violence. He attended Eli Whitney High School in Brooklyn, where he was a classmate of the soon-to-be-martyred rap legend Notorious B.I.G. As Jay-Z later remembered his childhood in one of his songs ("December 4th"), "I went to school, got good grades, could behave when I wanted/ But I had demons deep inside that would raise when confronted."
Carter turned to rap at a very young age as an escape from the drugs, violence and poverty that surrounded him in the Marcy Projects. In 1989, he joined the rapper Jaz-O—an older performer who served as a kind of mentor—to record a song called "The Originators," which won the pair an appearance on an episode of Yo! MTV Raps. It was at this point that Shawn Carter embraced the nickname Jay-Z, which was simultaneously an homage to Jaz-O, a play on Carter's childhood nickname of "Jazzy," and a reference to the J/Z subway station near his Brooklyn home. But even though he had a stage name, Jay-Z remained relatively anonymous until he and two friends, Damon Dash and Kareem Burke, founded their own record label, Roc-A-Fella Records, in 1996. In June of that year, Jay-Z released his debut album, Reasonable Doubt. Although the record only reached No. 23 on the Billboard charts, it is now considered a classic hip-hop album, featuring songs such as "Can't Knock the Hustle," featuring Mary J. Blige, and "Brooklyn's Finest," a collaboration with Notorious B.I.G. Reasonable Doubt established Jay-Z as an emerging star in hip-hop.
Two years later, Jay-Z achieved even broader success with the 1998 album Vol. 2 ... Hard Knock Life. The title track, which famously sampled its chorus from the Broadway musical Annie, became Jay-Z's most popular single to date and won him his first Grammy nomination. "Hard Knock Life" marked the beginning of a fruitful period in which Jay-Z would become the biggest name in hip-hop. Over the span of those years, the rapper released a slew of No. 1 albums and hit singles. His most popular songs from this period include "Can I Get A ...", "Big Pimpin'", "I Just Wanna Love U", "Izzo (H.O.V.A.)" and "03 Bonnie & Clyde", a duet with future bride Beyoncé Knowles.